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A Cytotoxic Neolignan from Schisandra propinqua (Wall.) Baill.
Journal of Integrative Plant Biology
Abstract
In the course of our study of bioactive natural products from Schisandra plants, we isolated a neolignan from an EtOAc extract of the stems of Schisandra propinqua (Wall.) Baill. The structure of the new compound was determined to be 4, 4-di (4-hydroxy-3-methoxyphenly)-2, 3-dimethylbutanol (compound 1) on the basis of 1H- and 13C-NMR spectra and 2D NMR methods. Eight known compounds, compounds 2-9, were also isolated and identified, of which compounds 3, 4, 6 and 9 were isolated for the first time from this plant. In addition, compounds 1-4 were evaluated for cytotoxicity by an 3-(4,5-dimethyl-2 thiazoyl)-2,5-diphenyl-2H-tetrazolium bromide (MTT) assay. Compound 1 showed significant potential cytotoxic ability in the bioassay.
(Managing editor: Wei Wang)
... The 7,7-diarylbutanol seco-lignans are an interesting class of lignans with both chemical and pharmacological importance. Cytotoxic, anti-HIV-1, and antioxidant activities have been previously reported for this class of natural products [12,20,21]. ...
From the aerial parts of Euphorbiagossypina var. coccinea Pax., eight new pregnane glycosides (euphogossypins A–H, 1–8) of the cynanforidine and deacetylmetaplexigenin aglycons, two new lignans (gossypilignans A and B, 9 and 10), and four known compounds, namely, the pregnane 12-O-benzoyldeaxcylmetaplexigenin (11), the lignan 9α-hydroxypinoresinol (12), and the flavonoids naringenin (13) and quercitrin (14) were isolated. The structure elucidation of the new compounds was carried out by a spectroscopic analysis, including HRMS, 1D (1H, 13C JMOD), and 2D NMR (HSQC, 1H–1H COSY, HMBC, and NOESY) experiments. The obtained pregnane glycosides were substituted with acetyl and benzoyl ester moieties, and sugar chains containing thevetose, cymarose, digitoxose, and glucose monosaccharides. All of the compounds are described for the first time from E. gossypina var. coccinea. The isolated pregnanes and lignans were tested for their antiproliferative activity on HeLa cells using the MTT assay; the compounds exerted no significant effect against the tumor cells.
... Macelignan had low cytotoxicity against HepG2 cells (IC 50 =62.7 ± 5.3 mg/mL; Figure 1A). This result is in agreement with the report that showed that macelignan had weak cytotoxicity against the HepG2 and MDA cells (21). However, miconazole had a strong cytotoxicity (IC 50 =5.9 ...
Ascosphaera apis is a bee pathogen that causes bee larvae infection disease, to which treatment is not yet well investigated. The aim of this study was to investigate antifungal susceptibility in vitro against A. apis and to identify a new antifungal agent for this pathogen through minimal inhibitory concentration (MIC) assay and western blot analysis. Macelignan had 1.56 and 3.125 μg/mL MIC against A. apis after 24 and 48 h, respectively, exhibiting the strongest growth inhibition against A. apis among the tested compounds (corosolic acid, dehydrocostus lactone, loganic acid, tracheloside, fangchinoline and emodin-8-O-β-D-glucopyranoside). Furthermore, macelignan showed a narrow-ranged spectrum against various fungal strains without any mammalian cell cytotoxicity. In spite of miconazole having powerful broad-ranged anti-fungal activity including A. apis, it demonstrated strong cytotoxicity. Therefore, even if macelignan alone was effective as an antifungal agent to treat A. apis, combined treatment with miconazole was more useful to overcome toxicity, drug resistance occurrence and cost effectiveness. Finally, HOG1 was revealed as a target molecule of macelignan in the anti-A. apis activity by inhibiting phosphorylation using S. cerevisiae as a model system. Based on our results, macelignan, a food-grade antimicrobial compound, would be an effective antifungal agent against A. apis infection in bees.
... In fact, some researchers have found that some natural compounds with scavenging free radical activities had advantages in procedures of cancer and inflammation (15)(16)(17)(18). In our previous study, it was found that some lignan and triterpene contents isolated from Schisandra propinqua showed modest cytotoxic activity in vitro against the growth of various human tumor cell lines (13,19). In the present study, we isolated four extracts and a lignan from stem of Schisandra propinqua, and investigated their antioxidant activities and free radical scavenging effects in different systems in vitro. ...
Schisandra propinqua (Wall.) Baill.(Schisandraceae) is widely used as a Chinese folk medicine. In this study, activity-guided fractionation of the ethanol extract from the stem of Schisandra propinqua led to the isolation of four extracts. Subsequently, a neolignan 4,4-di(4-hydroxy-3-methoxyphenly)-2,3-dimethylbutanol was isolated from the EtOAc part of the stem of Schisandra propinqua, the free radical scavenging activities of which were researched in vitro. The present work demonstrated that extracts and pure compound possessed scavenging activities to DPPH, superoxide anions and hydroxy radical, and could depress lipid peroxidation reaction induced by oxygen radical produced by the Fe2+/cysteine system in vitro. This suggests that the traditional application of Schisandra propinqua in China may be related to its antioxidant activities, and the EtOAc part of the stems of Schisandra propinqua can be utilized as an effective source of antioxidants.
Global Natural Product Social (GNPS) feature based networking was applied to follow the phytochemicals including 9 flavonoid glycosides, 6 catechins, and 3 flavonols in Huangjinya green tea. Further, a new 8-O-4′-type neolignan glycoside, camellignanoside A (1), together with 15 known compounds (2-16), were isolated through a variety of column chromatography, and the structure was elucidated extensively by UPLC-Q-TOF-MS2, 1H and 13C NMR, HSQC, HMBC, 1H-1H CCOY, ROESY, and NOESY, and circular dichroism (CD) spectroscopies. Compounds 1 and 2 showed acetylcolinesterase (AChE) inhibition activity with IC50 = 0.75 and 0.18 μM, respectively.
An isoform of NADPH oxidase (NOX), NOX2 is a superoxide-generating enzyme involved in diverse pathophysiological events. Although its potential as a therapeutic target has been validated, there is no clinically available inhibitor. Herein, NOX2-inhibitory activity was screened with the constituents isolated from Schisandra chinensis, which has been reported to have antioxidant and reactive oxygen species (ROS)-scavenging effects. Among the partitions prepared from crude methanolic extract, a chloroform-soluble partition showed the highest NOX2-inhibitory activity in PLB-985 cell-based NOX2 assay. A total of twenty nine compounds (1 - 29) were identified from the chloroform fraction, including two first isolated compounds; dimethyl-malate (25) and 2-(2-hydroxyacetyl) furan (27) from this plants. Of these constituents, two compounds (gomisin T, and pregomisin) exhibited an NOX2-inhibitory effect with the IC50 of 9.4 ± 3.6, and 62.9 ± 11.3 µM, respectively. They are confirmed not to be nonspecific superoxide scavengers in a counter assay using a xanthine–xanthine oxidase system. These findings suggest the potential application of gomisin T (6) and other constituents of S. chinensis to inhibit NOX2.
The sole species of the vascular plant family Austrobaileyaceae, Austrobaileya scandens, is endemic to the tropical rainforest of northeastern Queensland, Australia. A single lead-like enhanced fraction of A. scandens showed potent inhibition against human prostate cancer PC3 cells. Chemical investigation of this plant resulted in the isolation of two new aryltetralin lignans, austrobailignans 8 and 9 (1 and 2), and the synthetic compound nicotlactone B (3), newly identified as a natural product together with nine known lignans (4-12). Their structures were established on the basis of spectroscopic analyses. Absolute configurations of the new compounds were determined by quantum chemical electronic circular dichroism (ECD) calculations employing time-dependent density functional theory. The ECD calculations were also used to assign the absolute configuration of marphenol K (4) and revise the absolute configuration of kadsurindutin C (20). Ten out of the 12 isolated compounds inhibited the growth of PC3 cells with IC50 values ranging from micromolar to nanomolar. Marphenol A (5) was found for the first time to induce apoptosis and arrest the S cell cycle phase of PC3 cells.
A new neolignan, daphnelignan C (1), together with four known one, were isolated from the leaves of Daphne feddei levl. var. The structures of daphnelignan C (1) were elucidated by spectroscopic methods, including extensive 1-D and 2-D NMR techniques. All the five compounds were tested for their cytotoxicity. Compound daphnelignan C (1) showed significant potential cytotoxic ability and weak anti HIV-1 activities.
Due to their linear, freely rotatable, structure many natural 7,7-diaryl-8,8′-dimethylbutan-7′-ol lignans are reported without any stereochemical assignment. Analysis of synthetic 8,8′-dimethylbutanol lignans and analogues reveals significant differences between the NMR data of syn- and anti-isomers. This information was then used to determine the relative stereochemistry of the C-8 and C-8′ methyl groups in previously undefined natural products. © 2015 Phytochemical Society of Europe. Published by Elsevier B.V. All rights reserved.
Selectively functionalised 1,4-diarylbutane-1,4-diols have been shown to undergo a number of different reactions upon treatment with methanesulfonyl chloride and triethylamine. These led to three different sub-classes of lignans, depending on the nature of the aryl groups. Rearrangement leading to the corresponding 4,4-diarylbutanals is the most common transformation and these butanals can be reduced to give analogues of seco-lignans.
All the stereoisomers of butanol type 1,7-seco-2,7′-cyclolignane were stereoselectively synthesized by employing (S)- and (R)-Evans’ auxiliaries to construct the stereochemistry. (+)- and (−)-Kadangustin J and their diastereomers were also prepared. The optical purity of the synthesized butanol type 1,7-seco-2,7′-cyclolignane was more than 99%ee.All the stereoisomers of butanol type 1,7-seco-2,7'-cyclolignane with more than 99%ee were stereoselectively synthesized. (+)- and (-)-Kadangustin J and their diastereomers were also prepared.
Seven new dibenzocyclooctadiene lignans, named propinquain E-K, together with 11 known lignans were isolated from the ethanol extract of the roots of Schisandra propinqua subsp. sinensis. The structures of the new compounds were elucidated by spectroscopic methods, including ¹H- and ¹³C-NMR, 2D-NMR, HR ESI-MS, and CD spectra. Two dibenzocyclooctadienes revealed inhibitory effects on lymphocyte proliferation.
Four new neolignans, marphenols G-J (1-4), together with two known ones, were isolated from the leaves and stems of Schisandra wilsoniana. The structures of 1-4 were elucidated by spectroscopic methods, including extensive 1D- and 2D-NMR techniques. New compounds 1-4 were tested for their anti-human immunodeficiency virus (HIV)-1 activities and they showed weak bioactivities.
Two new neolignans, schilancifolignans D and E (1 and 2), together with eight known ones, were isolated from the leaves and stems of Schisandra lancifolia. The structures of 1 and 2 were elucidated by spectroscopic methods, including extensive 1D and 2D NMR techniques. Compounds 1 and 2 were tested for their anti-HIV-1 activities and cytotoxicity. Both showed significant potential cytotoxic ability and weak anti-HIV-1 activities.
A new nortriterpenoid, 20-hydroxymicrandilactone D (1) and a novel lignan glycoside, lancilignanside A (2) were isolated from leaves and stems of Schisandra lancifolia, together with three known nortriterpenoids (3-5) and nine known phenolics (6-14). The structures of new compounds 1 and 2 were determined by detailed analysis of their 1D and 2D NMR spectra, and chemical evidences. In addition, compounds 1-2, 6-7, and 9-11 showed anti-human immunodeficiency virus (HIV)-1 activities with 50% effective concentration (EC(50)) in the range of 3.0-99.0 microg/ml. Compound 12 was not bioactive in this assay with EC(50) more than 200 microg/ml.
Covering: 2005 to 2008.
Two new lignans, henricines A (1) and B (2), were isolated along with the eight known lignans, ganshisandrine (3), wulignan A(2) (4), epiwulignan A(1) (5), deoxyschisandrin (6), wulignan A(1) (7), epischisandrone (8), schisantherin A (9), and schisandrol A (10), from the stems of Schisandra henryi. The structures of the new compounds were elucidated based on the spectral analysis, including 1D and 2D NMR experiments.
Phytochemical investigation of Kadsura angustifolia led to the isolation and identification of 26 lignans and two triterpenoids, including 11 new lignans named kadangustins A-K (1-11). The structures and stereochemistry of 1-11 were elucidated by analysis of spectroscopic data. Except for 11 and 20, all the lignans were evaluated for their inhibitory activity against HIV-1. Binankadsurin A (19) showed anti-HIV activity with an EC50 value of 3.86 μM. © 2008 American Chemical Society and American Society of Pharmacognosy.
Eight dibenzocyclooctadiene lignans were isolated from the stems of Schisandra propinqua (Wall. )Hook. f. et Thoms. Their structures were elucidated as acetylgomisin R(1), angeloylgomisin R (2), gomisins A(3), B(4), N(S) and O(6) , 6-O-benzoylgomosin O(7) and schisantherin A(8) by spectral studies. Among them, compound 1 was a new one, compound 2 was discovered in the genus Schisandra for the first time and the others were originally isolated from Schisandra propinqua.
OBJECTIVE: To reveal the chemical constituents of Glycosmis citrifolia (Willd.) Lindl. METHODS: Chromatographic techniques were employed for isolation and purification, and the structures were identified by spectral analyses. RESULTS: Five compounds were isolated and identified as wogonin(I), vanillic acid(II), Glycosmisic acid[5-(2-carboxyvinyl)-2-(4-hydroxy-3-methoxyphenyl)-3- (hydroxymethyl)-7-methoxy-2, 3-dihydrobenzofuran, III, Glycoric acid (IV) and 4, 4′-dihydroxy-3, 3′-dimethoxy-trans-stilbene(V). CONCLUSION: All of the five compounds were isolated from this plant for the first time.
Nordihydroguaiaretic acid (NDGA, meso-1) possesses four phenolic hydroxyl groups. Treatment of NDGA with 0.50−4.1 equiv of dimethyl sulfate and 3.0−6.0 equiv of potassium carbonate in acetone at 56 °C gave nine methylated products. Eight of those mono-, di-, tri-, and tetra-O-methylated NDGAs were isolated in pure form, and their structures were identified unambiguously by spectroscopic methods. A preparative amount of tetramethyl NDGA M4N (10) was obtained in 99% yield from NDGA by use of 4.1 equiv of dimethyl sulfate for the methylation. Among the eight different methylated NDGAs (2−6 and 8−10), tetra-O-methyl-NDGA (10) showed the strongest anti-HIV activity (IC50 11 μM). Chemically synthesized 3‘-O-methyl-NDGA ((±)-2) showed identical anti-HIV activity (IC50 25 μM) to the lignan isolated from Creosote Bush. Lignans with methylated catecholic hydroxyl groups can be produced in large quantities with low cost. At drug concentrations below 30 μM, tetramethyl NDGA (10) was a stronger anti-HIV agent than mono- and dimethylated NDGAs.
Three new ent-atisane diterpenes, i.e., 17-hydroxy-ent-atisan-19-oic acid (1), 17-hydroxy-ent-atisan-19-oic acid methyl ester (2), and 16,17-dihydroxy-ent-atisan-19-al (3), together with five known phenolic compounds, i.e., gallic acid, ethyl gallate, protocatechuic acid, 3,4,4′-tri-O-methylellagic acid, and -tocopherol, and two other known compounds, i.e., trans-cinnamic acid and taraxerone, were isolated from the pericarp of Trewia nudiflora collected in Xishuangbanna, Yunnan Province, China. Their structures were elucidated by spectroscopic analysis including 1D- and 2D-NMR. Trace amounts of maytansinoids were isolated by antifungal-activity-guided fractionation and determined by LC-ESI-MS analysis; they were prominent antifungal constituents in the pericarp of Trewia nudiflora.
A tetrazolium salt has been used to develop a quantitative colorimetric assay for mammalian cell survival and proliferation. The assay detects living, but not dead cells and the signal generated is dependent on the degree of activation of the cells. This method can therefore be used to measure cytotoxicity, proliferation or activation. The results can be read on a multiwell scanning spectrophotometer (ELISA reader) and show a high degree of precision. No washing steps are used in the assay. The main advantages of the colorimetric assay are its rapidity and precision, and the lack of any radioisotope. We have used the assay to measure proliferative lymphokines, mitogen stimulations and complement-mediated lysis.
Phytochemical investigations of Tsoongiodendron odorum and Manglietiastrum sinicum, both Magnoliaceae, led to the isolation of twenty compounds in total. Among them, one was a new sesquiterpene, 11-O-oleoyl-beta-eudesmol (2), and another, 1-(3,4-dimethoxypheny)-4-(3,4-methylenedioxyphenyl)-2,3-dimethy lbutane (12) was isolated as a natural product for the first time. Moreover, 13C-NMR spectral data of isoguaiacin (16) are reported here for the first time. Structure elucidations for compounds reported here were mainly based on their spectral data. The ethanolic extracts of T. odorum and M. sinicum, and six pure compounds, 4(15)-eudesmen-11-ol (beta-eudesmol) (1), 1 beta-hydroxy-4(15),11(13)-eudesmadien-12,6 alpha-olide (reynosin) (3), 3,11(13)-eudesmadien-12,6 alpha-olide (alpha-cyclocostunolide) (5), erythro-1-(4-hydroxy-3-methoxyphenyl)-4-(3,4-methylenedioxyphenyl)-2,3- dimethylbutane (11), nectandrin-B (18), and syringaresinol (19), displayed considerable inhibition against platelet aggregation induced by AA, by ADP, or by PAF.
Three dibenzocyclooctadiene lignans were isolated from the stems of Schisandra propinqua (Wall.) Hook.f.et Thoms. Their structures were identified as interiotherin A (I), benzoylisogomisin O (II) and gomisin G (III) by spectroscopic analysis. Compound I was first discovered in Schisandra genus. Compounds II and III were originally isolated from S. propinqua.
The chemical constituents of Kadsura Longepedunculata collected from Zhejiang province were studied. Six compounds were isolated and their structures were elucidated based on physical and spectral analysis. Among them, one is a new compound, which is named kadsulactone acid (I) and the others are kadsulactone (II), (+)-anwulignan (III), mesodihydroguaiaretic acid (IV), d-epidalbacin(V) and beta-sitosterol (VI).
To isolate and characterize compounds from the stems of Schisandra propinqua.
Extracting with solvent, isolating by column chromatography and identifying by the spectroscopic methods.
Six dibenzocyclooctadiene lignans were isolated and identified as tigloylgomisin P(1), angeloylgomisin O(2), angeloylisogomisin O(3), kadsulignan L(4), (+/-) 5,8-epoxyl-6, 7-dimethyl-2',3',2",3"-dimethylenedioxy-4', 1"-dimethyl-1,2:3,4-dibenzo-1, 3-cyclooctadiene(5) and wuweizisu C(6).
Compounds 4 and 5 were the first two dibenzocyclooctadiene lignans with an 6,9-epoxy bridge cycle discovered in the genus Schisandra. The others were originally isolated from S. propinqua.
To investigate the chemical constituents of the dried buds of Lonicera confusa.
Chromatography and spectral analysis were respectively used to isolate and identify the constituents.
Seven compounds were isolated from the dried buds of L. confusa, and identified as rutin, quercetin, luteilin-7-O-beta-D-galactoside, lonicerin, chlorogenic acid, beta-sitosterol and tetratriacontane.
Rutin was isolated from the genus for the first time, and the others were isolated from the species for the first time.
To study the chemical constituents of the essential substance from Polygonum oriental. Method: Compounds were isolated with silica gel and polyamide chromatography and their structures were determined by spectral analysis and chemical evidence.
Six compounds were obtained and identified as myricitrin, luteolin, gallic acid, catechin, protocatechuic acid, p-hydroxycinnamic acid.
Six compounds were isolated from P. oriental for the first time.